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Glycyrrhizin
IUPAC name(3-β,20-β)-20-Carboxy-11-oxo-30-norolean-12-en-3-yl
2-O-β-D-glucopyranuronosyl-α-D-glucopyranosiduronic acid
Other namesGlycyrrhizin
Glycyrrhizinic acid
Glycyrrhizic acid
Identifiers
CAS number1405-86-3
SMILESOC1C(O)C(O)C (OC2C(O)C(O)C (C(O)=O)OC2OC3 [C@]
(C)(C)[C@@] (CC[C@]([C@@] (CC[C@]7(C)[C@@]
([H])6C[C@@](C)(C(O)=O)CC7) (C)C6=C5)(C) [C@@]([H])4
C5=O) ([H])[C@]4(C) CC3)OC1C(O)=O
Properties
Molecular formulaC42H62O16
Molar mass822.94 g/mol
Except where noted otherwise, data are given for
materials in their standard state
(at 25 C, 100 kPa)


Glycyrrhizin, glycyrrhizinic acid or glycyrrhizic acid, is the active principle of liquorice root. It is a powerful sweetener, 30–50 times as potent as sucrose (table sugar).

Chemically, glycyrrhizin is a triterpenoid glycosidic saponin. The acid form is not particularly water-soluble, but its ammonium salt is soluble in water at pH greater than 4.5.

Although sweet, the taste of glycyrrhizin is different from that of sugar. The sweetness of glycyrrhizin has a slower onset than sugar, and lingers in the mouth for some time. Additionally, its characteristic licorice flavor makes it unsuitable as a direct flavor substitute for sugar. Unlike the artificial sweetener aspartame, glycyrrhizin maintains its sweetness under heating.

In the United States, glycyrrhizin is classified as "generally recognized as safe" as a flavoring agent, although not as a sweetener. Glycyrrhizin is used as a flavoring in some candies, pharmaceuticals, and tobacco products.

In Japan, where concern over the safety of artificial sweeteners during the 1970s led to a shift towards plant-derived sugar substitutes, glycyrrhizin is a commonly used sweetener, often used in combination with another plant-based sweetener, stevia. However, glycyrrhizin appears to have some pharmacological side effects, and the Japanese government has asked its citizens to limit their consumption to 200 milligrams per day.

Health effects

Glycyrrhizin and other licorice root products have been used for numerous medical purposes, particularly treatment of peptic ulcers and as an expectorant. The triterpene derivative of glycyrrhizin, glycyrrhetinic acid, is itself effective in treatment of peptic ulcer. A synthetic analog, carbenoxolone, was developed in Britain. Both glycyrrhetinic acid and carbenoxolone have a modulatory effect on neural signaling through gap junction channels.

The most widely reported side effects of glycyrrhizin use are hypertension and edema (water retention). Deglycyrrhizinated licorice is a preparation used for treating ulcers which has had the glycyrrhizin removed in order to avoid the side effects.

Recently researchers have demonstrated that doses of licorice root extract, delivering the constituent glycyrrhizin in amounts similar to that contained in standard medical doses of the root, rapidly and significantly lowered levels of circulating testosterone in males.[1]

Liquorice consists of dried, peeled or unpeeled, root and stolons of Glycyrrhiza glabra, which belongs to the family leguminosae.

Why hypertension?

Glycyrrhizin inhibits the conversion of cortisol to cortisone by inhibiting the enzyme 11Beta Hydroxysteroid dehydrogenase.[2] As a result, cortisol levels are high within the collecting duct of the kidney. Cortisol has intrinsic mineralocorticoid properties (that is, it acts like aldosterone and increases sodium reabsorption) that work on ENaC channels in the collecting duct. Hypertension develops due to this mechanism of sodium retention. People often have high blood pressure with a low renin and low aldosterone blood level.

External links

Footnotes

1. ^ Glycyrrhiza: Licorice root and testosterone
2. ^ Quinkler M, Stewart PM. (2002). "Hypertension and the Corisol-Cortisone shuttle". J Clin Endocrinol Metab 88 (6): 2384–92. 


 •  • [ e]
Major families of biochemicals
Peptides | Amino acids | Nucleic acids | Carbohydrates | Lipids | Terpenes | Carotenoids | Tetrapyrroles | Enzyme cofactors | Steroids | Flavonoids | Alkaloids | Polyketides | Glycosides
Analogues of nucleic acids:Types of GlycosidesAnalogues of nucleic acids:
Bond: O-glycosidic bond | S-glycosidic bond | N-glycosidic bond
Geometry: α-Glycoside | β-Glycoside | 1,4-Glycoside | 1,6-Glycoside
Glycone: Glucoside | Fructoside | Glucuronide
Aglycone: Alcoholic glycoside | Anthraquinone glycoside | Coumarin glycoside | Cyanogenic glycoside | Flavonoid glycoside | Phenolic glycoside | Saponin | Cardiac glycoside | Steviol glycoside | Thioglycoside | Glycosylamine | Bufanolide | Cardenolide
IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. It is developed and kept up to date under the auspices of the International Union of Pure and Applied Chemistry (IUPAC).
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smiles

File extension: .smi
Type of format: chemical file format

The simplified molecular input line entry specification or SMILES
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A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. A chemical formula is also a short way of showing how a chemical reaction occurs.
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Molar mass, symbol M,[1] is the mass of one mole of a substance (chemical element or chemical compound).[2] It is a physical property which is characteristic of each pure substance.
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standard state of a material is its state at 1 bar (100 kilopascals exactly). This pressure was changed from 1 atm (101.325 kilopascals) by IUPAC in 1990.[1] The standard state of a material can be defined at any given temperature, most commonly 25 degrees Celsius,
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G. glabra

Binomial name
Glycyrrhiza glabra
L.

Liquorice or licorice (see spelling differences) (IPA:
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A sweetener is a food additive which adds the basic taste of sweetness to a food.

In Commonwealth English, "sweeteners" is usually used to refer to sugar substitutes.
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Sucrose (common name: table sugar, also called saccharose) is a disaccharide (glucose + fructose) with the molecular formula C12H22O11. Its systematic name is α-D-glucopyranosyl-(1→2)-β-D-fructofuranose.
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Sucrose (common name: table sugar, also called saccharose) is a disaccharide (glucose + fructose) with the molecular formula C12H22O11. Its systematic name is α-D-glucopyranosyl-(1→2)-β-D-fructofuranose.
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terpenoids, sometimes referred to as isoprenoids, are a large and diverse class of naturally occurring organic chemicals similar to terpenes, derived from five-carbon isoprene units assembled and modified in thousands of ways.
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Genin redirects here. For the Naruto ninja rank, see Genin (Naruto).


In chemistry, glycosides are certain molecules in which a sugar part is bound to some other part. Glycosides play numerous important roles in living organisms.
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Saponins are glycosides of steroids, steroid alkaloids (steroids with a nitrogen function) or triterpenes found in plants, especially in the plant skins where they form a waxy protective coating. Some authors distinguish a third class of saponin, the alkaloid saponins.
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Ammonium is also an old name for the Siwa Oasis in western Egypt.


The ammonium cation is a positively charged polyatomic cation of the chemical formula NH4+. It has a molecular mass of 18.
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This article is about the term salt as referred to in chemistry. For the everyday meaning, see salt or its main ingredient, sodium chloride. For other meanings of the word salt, see salt (disambiguation).

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    pH is a measure of the acidity or alkalinity of a solution. Aqueous solutions at 25 ℃ with a pH less than seven are considered acidic, while those with a pH greater than seven are considered basic (alkaline). The pH of 7.
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    Aspartame (or APM) (IPA: /ˈæ.spɚˌteɪm/ or /əˈspɑɹˌteɪm/
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    Tobacco is an agricultural product processed from the fresh leaves of plants in the genus Nicotiana.

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    Stevia

    Species

    About 150 species, including:
    Stevia eupatoria
    Stevia ovata
    Stevia plummerae
    Stevia rebaudiana
    Stevia salicifolia
    Stevia serrata

    Stevia
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    MeSH D010437

    A peptic ulcer, also known as PUD or peptic ulcer disease[1] is an ulcer of an area of the gastrointestinal tract that is usually acidic and thus extremely painful.
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    Glycyrrhetinic acid is a pentacyclic triterpenoid amyrin derivative obtained from the hydrolysis of glycyrrhizic acid.[1] It is used in flavouring and it masks the bitter taste of drugs like aloe and quinine.
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    Carbenoxolone, a synthetic derivative of glycyrrhizinic acid, is a licensed drug (in the UK) for oesophageal ulceration and inflammation. Other uses include treatment of oral and perioral lesions.
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    A gap junction or nexus is a junction between certain animal cell-types that allows different molecules and ions, mostly small intracellular signaling molecules (intracellular mediators), to pass freely between cells. The junction connects the cytoplasm of cells.
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    Hypertension
    Classification & external resources

    ICD-10 I 10. ,I 11. ,I 12. ,
    I 13. ,I 15.
    ICD-9 401.x

    OMIM 145500
    DiseasesDB 6330
    MedlinePlus 000468
    eMedicine med/1106   ped/1097 emerg/267


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